TALLAHASSEE — In the Capitol, everyone needs an insider.
Even the ultimate outsider, Gov. Rick Scott.
As a candidate, Scott bashed Tallahassee's special interests and derided the business-as-usual style of state politicians.
As governor, he needed to make nice with the Capitol crowd that largely runs the town.
He needed Hayden Dempsey — a 43-year-old lobbyist, Jeb Bush hand and an early Scott supporter — to bring the outsider and the insiders together.
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Jubilant after defeating Capitol favorite Bill McCollum in the August primary, Scott declared at his victory celebration: "Tonight we have sent a clear message to the Washington insiders — to the Tallahassee insiders — and the special interests that fund both of them. The message: We're going to clean house and hold government accountable."
He added: "The dealmakers are crying in their cocktails."
After the election, Dempsey was left to make peace.
He had an idea: invite legislators to the governor's mansion for informal chats over coffee or dinner. Build relationships. The private events irritated the press but helped Scott get to know key legislators and caucuses.
"I guess it was my idea, but it was always his desire to get to know them better, and a lot of them reached out to me also," said Dempsey, who as special counsel and legislative affairs director earns $140,000 a year.
Critics say Scott's legislative successes amount to a handful of original initiatives: modest tax cuts for businesses and property owners, drug-testing of welfare recipients and reshaping the state's land-planning agency, the Department of Community Affairs. The hungry Republican super-majority, they say, would have passed reforms to education, employee pensions and property insurance without him.
Still, Dempsey considers Scott's gains huge victories.
Take the drug-testing bill. The Legislature's version would have applied only to felons recently convicted of drug abuse. But Scott wanted all recipients tested, so Dempsey approached sponsors Sen. Steve Oelrich, R-Cross Creek, and Rep. Jimmie Smith, R-Inverness. Dempsey calls it "education."
"We needed to justify our rationale. We talked to them about the policy behind it," he said.
Scott's attempt to reduce a $170 million budget deficit at the Agency for Persons with Disabilities didn't work out as well. Scott issued an emergency order in April to cut rates charged by group homes and case workers who help the developmentally disabled.
Dempsey said Scott had few options. The one he chose sparked protests at the Capitol. Scott eventually rescinded the order.
"I think on this or any other issue you're going to find that when this governor is presented with a problem, he's not going to shirk out of political fear over making tough decisions," he said. "The one lesson that every governor learns is you've got to communicate. You've got to communicate with legislators, with stakeholders, and seek input."
Dempsey's work impressed Scott — who said in an interview that Dempsey "did a real good job" — but not everyone.
Sen. Dennis Jones, R-Seminole, said he has known Dempsey for years but didn't hear a peep from the governor's senior staff all session. The oversight is surprising, he said, as he chaired the Regulated Industries Committee and sponsored legislation on casino resorts, "the only bill that actually created jobs in the whole legislative session."
"He's an insider, but he's very low key. I mean, this is not bringing in a Brian Ballard," Jones said, referencing one of the state's most influential lobbyists and finance chairman of Scott's inauguration committee.
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Dempsey has been here before, spending three years in Bush's administration. He loved the work but not the demanding hours.
Dempsey wanted more time with daughters Emily, 14, and Caroline, 11, whom he raises with former wife and Second Circuit Judge Angela Cote Dempsey.
He left his legislative affairs job in 2002 for the private sector. Bush has no hard feelings.
"Great guy," he wrote in an e-mail. "Smart, personable, knowledgeable. He is an asset to the governor."
Dempsey's first stop was GrayRobinson, where he worked with fellow Winter Park native and now-House Speaker Dean Cannon. Dempsey moved to Greenberg Traurig, where he lobbied on behalf of clients like UnitedHealth Group for seven years.
He and Scott first met in the firm's Orlando office in May 2010, per Dempsey's request, not long after Scott declared his candidacy. His focus on jobs impressed Dempsey, a lifelong conservative.
The pair worked closely during session, often meeting several times a day to discuss history behind legislation or progress on priorities.
There was time for other stuff, too. Scott, whose two daughters are married and in their 20s, offers Dempsey advice for raising young girls. When Dempsey and Emily disagreed on which high school she should attend, he thought up a compromise from talking with Scott.
Emily could go to Leon High so long as she upheld the terms of a lofty contract: straight A's, a slate of honors and Advanced Placement courses, volleyball and a non-sports activity.
Creating measurements. Holding people accountable.
Pretty much Scott's campaign stump speech.
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Scott's new chief of staff and political veteran Steve MacNamara starts Tuesday.
Rumors of Dempsey's departure started weeks before that.
Dempsey has strong connections within the Legislature, but MacNamara's run deeper. He most recently served as chief of staff to Senate President Mike Haridopolos. He also was chief of staff under House Speaker John Thrasher in the late '90s.
Scott did not ask for a time commitment when he hired Dempsey, and Dempsey didn't give him one, he said. That ambiguity leaves open a return to the private sector.
He hasn't ruled out an eventual return to Greenberg Traurig, which has not removed a sign reserving Dempsey's parking space in a garage a few blocks from the Capitol.
"I want to do whatever I can to make sure that Gov. Scott's successful," he said. "My two considerations about what happens in the future are: one, his success, and two, my obligations to my daughters."
Still, Dempsey insists he and MacNamara had a solid working relationship this session and could work well together.
A summer exit, however, would add him to the ranks of departed senior staffers Mary Anne Carter, policy chief, and Mike Prendergast, Scott's chief of staff who was reassigned to an agency job.
Sometimes it's just natural for people to leave, Dempsey said.
"I said coming out of Jeb's administration, 'That's the greatest job I'll ever have,' " he said. "And at some point when I leave here I'm going to say, 'God, that was the greatest job I ever had.' "
Times researcher Caryn Baird and Times/Herald staff writer Michael C. Bender contributed to this report. Katie Sanders can be reached at firstname.lastname@example.org.